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Key Documents

T2952

Sigma-Aldrich

Tetrabenazine

≥98% (HPLC), solid

Synonym(s):

9,10-Dimethoxy-1,3,4,6,7,11b-hexahydro-3-isobutyl-(rel 3R,11bR)-2H-benzo[a]quinolizin-2-one

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About This Item

Empirical Formula (Hill Notation):
C19H27NO3
CAS Number:
Molecular Weight:
317.42
Beilstein:
40090
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL
H2O: insoluble

originator

Roche

storage temp.

2-8°C

SMILES string

COc1cc2CCN3C[C@@H](CC(C)C)C(=O)CC3c2cc1OC

InChI

1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3/t14-,16-/m1/s1

InChI key

MKJIEFSOBYUXJB-GDBMZVCRSA-N

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Application

Tetrabenazine has been used for dopamine uptake assays in mouse brain cells1. Tetrabenazine has also been used for non-specific binding assays in postnuclear supernatants derived from PC-12 and CV-1 cells2.

Biochem/physiol Actions

Tetrabenazine is a reversible type 2 vesicular monoamine transporter (VMAT) inhibitor. It depletes dopamine stores.

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Tetrabenazine is soluble in DMSO at a concentration that is greater than 10 mg/ml and is insoluble in water.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yelena Ugolev et al.
The Journal of biological chemistry, 288(45), 32160-32171 (2013-09-26)
Vesicular monoamine transporter 2 (VMAT2) transports monoamines into storage vesicles in a process that involves exchange of the charged monoamine with two protons. VMAT2 is a member of the DHA12 family of multidrug transporters that belongs to the major facilitator
Victor L Villemagne et al.
Neuro-degenerative diseases, 10(1-4), 161-165 (2012-01-21)
The noninvasive evaluation of nigrostriatal dopaminergic integrity by PET can provide useful information for the differential diagnosis between dementia with Lewy bodies (DLB) and Alzheimer's disease (AD). To evaluate the diagnostic potential of imaging striatal monoaminergic terminal integrity with the
Michael P Dalton et al.
eLife, 12 (2024-03-22)
The vesicular monoamine transporter 2 (VMAT2) is a proton-dependent antiporter responsible for loading monoamine neurotransmitters into synaptic vesicles. Dysregulation of VMAT2 can lead to several neuropsychiatric disorders including Parkinson's disease and schizophrenia. Furthermore, drugs such as amphetamine and MDMA are
Mahabuba Jahan et al.
EJNMMI research, 1(1), 33-33 (2012-01-05)
Fluorine-18 dihydrotetrabenazine [DTBZ] analogues, which selectively target the vesicular monoamine transporter 2 [VMAT2], have been extensively studied for in vivo quantification of beta cell mass by positron-emission tomography [PET]. This study describes a novel deuterated radioligand [18F]fluoroethyl [FE]-DTBZ-d4, aimed to
Catarina A Owesson-White et al.
Journal of neurochemistry, 121(2), 252-262 (2012-02-03)
Mesolimbic dopamine neurons fire in both tonic and phasic modes resulting in detectable extracellular levels of dopamine in the nucleus accumbens (NAc). In the past, different techniques have targeted dopamine levels in the NAc to establish a basal concentration. In

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